700360-99-2

Upstream product

• 54594-06-8 D-allylglycine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 700360-94-7 [(R)-1-((S)-Hydroxy-thiazol-2-yl-methyl)-but-3-enyl]-(4-methoxy-benzyl)-carbamic acid tert-butyl ester 
• 774578-68-6 2-[tert-butoxycarbonyl-(4-methoxy-benzyl)-amino]-pent-4-enoic acid methyl ester 
• 1012322-69-8 (R)-2-{[1-(4-Methoxy-phenyl)-meth-(Z)-ylidene]-amino}-pent-4-enoic acid methyl ester 
• 188195-08-6 (R)-2-(4-methoxy-benzylamino)-pent-4-enoic acid methyl ester 
• 81136-73-4 (R)-2-allylglycine methyl ester 
• 700360-97-0 [(R)-1-((S)-Benzyloxy-thiazol-2-yl-methyl)-but-3-enyl]-carbamic acid tert-butyl ester 

Downstream Products

• 1054689-88-1 ((1R,5S,6S)-6-Benzyloxy-5-hydroxy-cyclohex-3-enyl)-carbamic acid tert-butyl ester 
• 700361-02-0 [6-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohex-3-enyl]-carbamic acid tert-butyl ester 
• 700361-03-1 [(1R,2S,3S,4R,5R)-2-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-4,5-dihydroxy-cyclohexyl]-carbamic acid tert-butyl ester 
• 700361-04-2 [(3aR,5R,6S,7R,7aS)-6-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2,2-dioxo-hexahydro-2λ⁶-benzo[1,3,2]dioxathiol-5-yl]-carbamic acid tert-butyl ester 
• 700361-01-9 ((1R,2S,3S)-1-Allyl-2-benzyloxy-3-hydroxy-pent-4-enyl)-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

Synthesis of a protected enantiomerically pure 2-deoxystreptamine derivative from D-allylglycine

A diastereoselective synthetic route from D-allylglycine to the enantiopure (protected) 2-deoxystreptamine derivative 14 is presented. Key steps involve two consecutive chain extensions - with crucial stereodirective roles for the amino protective groups, ring closure by olefin metathesis, face selective dihydroxylation, cyclic sulfate formation and finally opening with azide. The resulting 2-deoxystreptamine derivative is ideally protected for the preparation of 4,5- or 4,6-linked aminoglycoside antibiotics.